Flavonoid deactivation of excited state flavins: reaction monitoring by mass spectrometry

Kevin André Jurgen Huvaere; Bart Sinnaeve; Jan Van Bocxlaer; Leif Horsfelt Skibsted

doi:10.1021/jf301823h

Flavonoid deactivation of excited state flavins: reaction monitoring by mass spectrometry

Kevin André Jurgen Huvaere, Bart Sinnaeve, Jan Van Bocxlaer, Leif Horsfelt Skibsted

17 Citations (Scopus)

Abstract

Flavin mononucleotide (FMN, as a B₂ vitamin model) was shown to induce dimerization of flavonoids (flavanone, apigenin, naringenin, eriodictyol, taxifolin, catechin, kaempferol, luteolin, quercetin, rutin, and seven smaller model phenols studied) as the major photoreaction, when aqueous solutions were exposed to visible light using a new, real-time electrospray ionization mass-spectrometric (ESI-MS) technique supported by LC-MS and MS² analysis. Electrophilic intermediates such as transient radical cations, o-quinones, and p-quinone methide were proposed to be involved in the coupling process. The C₃-OH in flavon-3-ols gave rise to atypical compounds such as a depside or a dioxane-linked dimer. Flavonoid dimers, formed in vegetal extracts added to food during storage in light and for which structures are proprosed based on MS and MS², may affect colloidal stability, color, astringency, and antioxidative capacity.

Original language	English
Journal	Journal of Agricultural and Food Chemistry
Volume	60
Issue number	36
Pages (from-to)	9261-9272
Number of pages	12
ISSN	0021-8561
DOIs	https://doi.org/10.1021/jf301823h
Publication status	Published - 12 Sept 2012

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title = "Flavonoid deactivation of excited state flavins: reaction monitoring by mass spectrometry",

abstract = "Flavin mononucleotide (FMN, as a B2 vitamin model) was shown to induce dimerization of flavonoids (flavanone, apigenin, naringenin, eriodictyol, taxifolin, catechin, kaempferol, luteolin, quercetin, rutin, and seven smaller model phenols studied) as the major photoreaction, when aqueous solutions were exposed to visible light using a new, real-time electrospray ionization mass-spectrometric (ESI-MS) technique supported by LC-MS and MS2 analysis. Electrophilic intermediates such as transient radical cations, o-quinones, and p-quinone methide were proposed to be involved in the coupling process. The C3-OH in flavon-3-ols gave rise to atypical compounds such as a depside or a dioxane-linked dimer. Flavonoid dimers, formed in vegetal extracts added to food during storage in light and for which structures are proprosed based on MS and MS2, may affect colloidal stability, color, astringency, and antioxidative capacity.",

author = "Huvaere, {Kevin Andr{\'e} Jurgen} and Bart Sinnaeve and Bocxlaer, {Jan Van} and Skibsted, {Leif Horsfelt}",

year = "2012",

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doi = "10.1021/jf301823h",

language = "English",

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TY - JOUR

T1 - Flavonoid deactivation of excited state flavins

T2 - reaction monitoring by mass spectrometry

AU - Huvaere, Kevin André Jurgen

AU - Sinnaeve, Bart

AU - Bocxlaer, Jan Van

AU - Skibsted, Leif Horsfelt

PY - 2012/9/12

Y1 - 2012/9/12

N2 - Flavin mononucleotide (FMN, as a B2 vitamin model) was shown to induce dimerization of flavonoids (flavanone, apigenin, naringenin, eriodictyol, taxifolin, catechin, kaempferol, luteolin, quercetin, rutin, and seven smaller model phenols studied) as the major photoreaction, when aqueous solutions were exposed to visible light using a new, real-time electrospray ionization mass-spectrometric (ESI-MS) technique supported by LC-MS and MS2 analysis. Electrophilic intermediates such as transient radical cations, o-quinones, and p-quinone methide were proposed to be involved in the coupling process. The C3-OH in flavon-3-ols gave rise to atypical compounds such as a depside or a dioxane-linked dimer. Flavonoid dimers, formed in vegetal extracts added to food during storage in light and for which structures are proprosed based on MS and MS2, may affect colloidal stability, color, astringency, and antioxidative capacity.

AB - Flavin mononucleotide (FMN, as a B2 vitamin model) was shown to induce dimerization of flavonoids (flavanone, apigenin, naringenin, eriodictyol, taxifolin, catechin, kaempferol, luteolin, quercetin, rutin, and seven smaller model phenols studied) as the major photoreaction, when aqueous solutions were exposed to visible light using a new, real-time electrospray ionization mass-spectrometric (ESI-MS) technique supported by LC-MS and MS2 analysis. Electrophilic intermediates such as transient radical cations, o-quinones, and p-quinone methide were proposed to be involved in the coupling process. The C3-OH in flavon-3-ols gave rise to atypical compounds such as a depside or a dioxane-linked dimer. Flavonoid dimers, formed in vegetal extracts added to food during storage in light and for which structures are proprosed based on MS and MS2, may affect colloidal stability, color, astringency, and antioxidative capacity.

U2 - 10.1021/jf301823h

DO - 10.1021/jf301823h

M3 - Journal article

C2 - 22889117

SN - 0021-8561

VL - 60

SP - 9261

EP - 9272

JO - Journal of Agricultural and Food Chemistry

JF - Journal of Agricultural and Food Chemistry

IS - 36

ER -

Flavonoid deactivation of excited state flavins: reaction monitoring by mass spectrometry

Abstract

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